Journal
ORGANIC LETTERS
Volume 24, Issue 34, Pages 6316-6320Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02535
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Funding
- National Natural Science Foundation of China [22071059]
- Program for Professor of Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Learning
- East China Normal University (ECNU)
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This study reports an electrophile-modulated aromatization reaction of highly functionalized cyclopropanes, which can produce structurally diverse benzoisocoumarins with the formation of both benzenoid and alpha-pyrone rings under mild conditions. The study also reveals the crucial role of neighboring olefinic substituents in determining whether a 1,2-shift of the ester group follows the cyclopropane ring expansion.
Reported herein is an electrophile-modulated aromatization reaction of highly functionalized cyclopropanes to structurally diverse benzoisocoumarins featuring concurrent formation of the benzenoid and alpha-pyrone rings under mild conditions. An aromatization reaction of the proposed benzonorcaradiene intermediates prepared independently revealed a crucial role of the neighboring olefinic substituents in determining whether the cyclopropane ring expansion is followed by a 1,2-shift of the ester group.
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